248. Enantioselective Gold(I)-Catalyzed Vinylogous [3 + 2] Cycloaddition between Vinyldiazoacetates and Enol Ethers

Authors: John F. Briones and Huw M. L. Davies

J. Am. Chem. Soc.,

2013, 135 (36), 13314–13317

056

The reaction of vinyldiazoacetates with enol ethers catalyzed by the binuclear gold complex (R)-DTBMSegphos(AuCl)2 activated by silver hexafluoroantimonate results in a highly enantioselective [3 + 2] cycloaddition. The [3 + 2] cycloaddition proceeds with dynamic kinetic resolution when the enol ether is a 4-substituted 1-(methoxymethylene)cyclohexane. The reaction is initiated by nucleophilic attack of the vinyl ethers at the vinylogous position of the gold vinylcarbene intermediate.

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